公开(公告)号：KR1020080065722A

公开(公告)日：2008-07-15

申请号：KR1020070002715

申请日：2007-01-10

Applicant: 한국화학연구원

Inventor： 전동주 ,  노재성 ,  송종환 ,  이계형 ,  김익연 ,  박창민 ,  소원영 ,  이지선 ,  김은주 ,  강남숙 ,  천혜경 ,  조영식 ,  송진숙 ,  배명애 ,  김지현 ,  조중명 ,  노성구 ,  현영란 ,  이철순 ,  이재일 ,  유성은

IPC: C07D231/12 ,  C07D401/04 ,  C07D403/10 ,  C07D413/04

Abstract: A novel compound is provided to show excellent activity on PDE-4 enzymes and high selectivity on other PDE enzymes, thereby being used as a therapeutic agent of inflammation related diseases, arthritis, atopic dermatitis, leukemia, various cancers and degenerative brain diseases with little side effects. A 1-[1-(3,4-dialkoxyphenyl)-alkyl]-1H-pyrazole compound is represented by a formula(1) and is prepared by reacting a halo-benzyl compound represented by a formula(2) with a pyrazole compound represented by a formula(3). In the formula(1), each R1 and R2 is independently H, linear or branched saturated or unsaturated C1-7 alkyl which may be substituted or unsubstituted by halogen, C3-7 cycloalkyl, (C3-7)cycloalkyl(C1-7)alkyl, aryl or heteroaryl, ar(C1-5)alkyl, or ar(C1-5)alkoxy, or the R1 and R2 may be linked to each other by C1-3 alkylene; each R3, R4 and R5 is independently H, phenyl, pyridinyl, N-oxypyridinyl, linear or branched saturated and unsaturated C1-7 alkyl, C3-7 cycloalkyl, (C3-10)cycloalkyl(C1-7)alkyl, halogen, cyano, nitro, amino, mono- or di(C1-7)alkylamino, mono or di(C1-7)alkylaminocarbonyl, C3-7 cycloalkylamino, 3 to 7-membered saturated or unsaturated hetero-ring including O, N or S, guanidinyl, ureido, benzyl, benzyloxy, formyl, C1-7 alkanoyl, C1-7 alkoxy, (C1-7)alkoxy(C1-7)alkyl, hydroxy(C1-7)alkyl, carboxyl, or (C1-7)alkoxycarbonyl; R6 is linear or branched saturated and unsaturated C1-7 alkyl, C3-7 cycloalkyl, (C3-10)cycloalkyl(C1-7)alkyl, phenyl, phenoxy, benzyl, benzyloxy, C1-7 alkoxy, or (C1-7)alkoxy(C1-7)alkyl. A pharmaceutical composition for treating or preventing diseases related to airway inflammation, arthritis, atopic dermatitis, leukemia, cancer or degenerative brain diseases comprises the 1-[1-(3,4-dialkoxyphenyl)-alkyl]-1H-pyrazole derivative as an effective ingredient.

Abstract translation: 提供了一种新型化合物，以显示对PDE-4酶的优异活性和对其他PDE酶的高选择性，从而被用作炎症相关疾病，关节炎，特应性皮炎，白血病，各种癌症和退行性脑病的治疗剂 效果。 1-（1-（3,4-二烷氧基苯基） - 烷基] -1H-吡唑化合物由式（1）表示，通过式（2）表示的卤代苄基化合物与吡唑化合物 由公式（3）表示。 在式（1）中，每个R 1和R 2独立地为H，可被卤素取代或未取代的直链或支链饱和或不饱和C 1-7烷基，C 3-7环烷基，（C 3-7）环烷基（C 1-7） 烷基，芳基或杂芳基，芳（C 1-5）烷基或芳（C 1-5）烷氧基，或者R 1和R 2可以被C 1-3亚烷基相互连接; 每个R 3，R 4和R 5独立地为H，苯基，吡啶基，N-氧代吡啶基，直链或支链饱和和不饱和C 1-7烷基，C 3-7环烷基，（C 3-10）环烷基（C 1-7）烷基，卤素，氰基 ，硝基，氨基，单或二（C1-7）烷基氨基，单或二（C1-7）烷基氨基羰基，C3-7环烷基氨基，3至7元饱和或不饱和杂环，包括O，N或S，胍基 （C 1-7）烷基，羟基（C 1-7）烷基，羧基或（C 1-7）烷氧基羰基;（C 1-7）烷氧基， R6是直链或支链饱和和不饱和的C1-7烷基，C3-7环烷基，（C3-10）环烷基（C1-7）烷基，苯基，苯氧基，苄基，苄氧基，C1-7烷氧基或（C1-7） 烷氧基（C 1-7）烷基。 用于治疗或预防与气道炎症，关节炎，特应性皮炎，白血病，癌症或退行性脑疾病相关的疾病的药物组合物包括1- [1-（3,4-二烷氧基苯基） - 烷基] -1H-吡唑衍生物作为有效的 成分。

公开(公告)号：KR100753017B1

公开(公告)日：2007-08-30

申请号：KR1020060046860

申请日：2006-05-25

Applicant: 한국화학연구원

Inventor： 노재성 ,  전동주 ,  송종환 ,  이계형 ,  박창민 ,  소원영 ,  강남숙 ,  홍석주 ,  천혜경 ,  조영식 ,  김기영 ,  배명애 ,  송진숙 ,  노성구 ,  현영란 ,  이운영 ,  김용은 ,  강봉균 ,  이혜련 ,  유성은

IPC: A61K31/437 ,  A61P35/00

Abstract: A pharmaceutical composition for treating or preventing arthritis, atopic dermatitis, tumor and degenerative brain diseases comprising 7-(3,4-Dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidine compounds is provided to inhibit activity of PDE-4(phosphodiesterase-4) and reduce side effects such as vomiting by reducing HARBS(high-affinity rolipram binding sites) affinity. The pharmaceutical composition for treating or preventing arthritis, atopic dermatitis, tumor and degenerative brain diseases comprises 7-(3,4-Dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidine compounds represented by the formula(1), wherein R1 and R2 are independently hydrogen atom, linear or branched saturated or unsaturated (C1-C7)alkyl, linear or branched saturated or unsaturated (C1-C7)alkyl containing halogen atom, (C3-C7)cycloalkyl, 3-membered to 7-membered heterocycloalkyl containing oxygen, nitrogen or sulfur in a hetero aromatic ring, (C4-C10)cycloalkyl(C1-C7)alkyl, 3-membered to 7-membered heterocycloalkyl(C1-C7)alkyl containing oxygen, nitrogen or sulfur in a hetero ring, phenyl, benzyl or allyl group; R3 is hydrogen atom, halogen atom, formyl, linear or branched and saturated or unsaturated (C1-C7)alkyl, (C1-C7)alkylketone, (C1-C7)alkoxy, (C1-C7)alkoxy (C1-C7)alkyl, hydroxy(C1-C7)alkyl group, carboxylic acid, carboxyl(C1-C7)alkylester, carboxyl(C1-C7)alkylamide, amino, or mono or di(C1-C7)alkylaminocarbonyl; and R4 is hydrogen atom, formyl, linear or branched saturated or unsaturated (C1-C7)alkyl, (C3-C7)cycloalkyl, (C1-C7)alkoxy, (C1-C7)alkoxy (C1-C7)alkyl, hydroxy(C1-C7)alkyl ketone, (C1-C10)alkylcarboxylic acid, carboxyl(C1-C10)alkylester, carboxyl(C1-C10)alkylamide, amino, mono or di(C1-C7)alkylamino, mono or di(C1-C7)alkylaminocarbonyl, (C3-C7)cycloalkylamine, morpholine, morpholine oxide, piperidine, piperazine, piperazine oxide or aryl group.

Abstract translation: 用于治疗或预防关节炎，特应性皮炎，肿瘤和退行性脑疾病，其包括7-（3,4-二烷氧基） - 吡唑并提供[1,5-a]嘧啶化合物抑制PDE-4的活性（phosphodiesterase-的药物组合物 4）并通过减少HARBS（高亲和力咯利普兰结合位点）亲和力来减少副作用，例如呕吐。 用于治疗或预防关节炎，特应性皮炎，肿瘤和退行性脑疾病的药物组合物包含7-（3,4-二烷氧基） - 吡唑并[1,5-a]嘧啶化合物由式（1）表示，其中R1和R2 （C 1 -C 7）烷基，含有卤素原子的直链或支链饱和或不饱和（C 1 -C 7）烷基，（C 3 -C 7）环烷基，含有3至7元杂环烷基的3元至7元杂环烷基 （C4-C10）环烷基（C1-C7）烷基，在杂环中含有氧，氮或硫的3元至7元杂环烷基（C1-C7）烷基，苯基 ，苄基或烯丙基; （C 1 -C 7）烷基，（C 1 -C 7）烷氧基，（C 1 -C 7）烷氧基（C 1 -C 7）烷基，（C 1 -C 7）烷氧基， （C 1 -C 7）烷基，羧酸，羧基（C 1 -C 7）烷基酯，羧基（C 1 -C 7）烷基酰胺，氨基或单或二（C 1 -C 7）烷基氨基羰基; （C 1 -C 7）烷基，（C 3 -C 7）环烷基，（C 1 -C 7）烷氧基，（C 1 -C 7）烷氧基（C 1 -C 7）烷基，羟基（C 1 -C 7）烷基， C1-C7）烷基酮，（C1-C10）烷基羧酸，羧基（C1-C10）烷基酯，羧基（C1-C10）烷基酰胺，氨基，单或二（C1-C7）烷基氨基，单或二（C1-C7 ）烷基氨基羰基，（C3-C7）环烷基胺，吗啉，氧化吗啉，哌啶，哌嗪，哌嗪氧化物或芳基。

公开(公告)号：KR100689961B1

公开(公告)日：2007-03-08

申请号：KR1020050018325

申请日：2005-03-04

Applicant: 한국화학연구원

Inventor： 노재성 ,  전동주 ,  송종환 ,  이계형 ,  정준원 ,  박창민 ,  정순민 ,  김지영 ,  강남숙 ,  홍석주 ,  천혜경 ,  남지연 ,  장범수 ,  곽현정 ,  송진숙 ,  허준영 ,  양승돈 ,  전영호 ,  노성구 ,  이태규 ,  현영란 ,  조중명 ,  허용석 ,  윤정민 ,  유성은

IPC: C07D277/42 ,  A61P11/06 ,  A61P25/28

Abstract: 본 발명은 하기의 화학식 1로 표시되는 신규한 4-(3,4-디알콕시페닐)-2-아미노티아졸 화합물 또는 그의 약제학적으로 허용 가능한 염, 이의 제조 방법 및 이를 유효성분으로 함유하는 것을 특징으로 하는 천식 및 만성폐쇄성 폐질환(Chronic Obstructive Pulmonary Disease)을 포함한 염증관련 질환의 치료 및 알쯔하이머를 포함한 중추신경계통 질환의 치료, 예방을 위한 약제학적 조성물에 관한 것이다.
[화학식 1]

4-(3,4-디알콕시페닐)-2-아미노티아졸, PDE-4, 천식, 만성폐쇄성 폐질환, 염증관련 질환, 중추신경계 질환, 알쯔하이머.

公开(公告)号：KR1020040092186A

公开(公告)日：2004-11-03

申请号：KR1020030026416

申请日：2003-04-25

Applicant: 한국화학연구원

Inventor： 전동주 ,  김형래 ,  송종환 ,  박관용 ,  정순민 ,  황인택

IPC: A01N43/90

Abstract: PURPOSE: Provided are 9-(5-isoxazolemethoxyphenyl)imino-8-thia-1,6-diazabicyclo(4.3.0)nonan-7-one derivatives which have herbicidal activity and a herbicidal composition containing the same as active ingredient. The derivatives have high stability to rice and excellent herbicidal effect. CONSTITUTION: 9-(5-isoxazolemethoxyphenyl)imino-8-thia-1,6-diazabicyclo(4.3.0)nonan-7-one derivative is represented by the formula(1), wherein R is C1-C5 alkyl group, phenyl group or substituted phenyl group in which the substituted phenyl group has a substituent selected from C1-C3 alkoxy group, halogen atom, cyano group and carboxylic acid ester group. The herbicidal composition is characterized by containing the 9-(5-isoxazolemethoxyphenyl)imino-8-thia-1,6-diazabicyclo(4.3.0)nonan-7-one derivative as active ingredient.

Abstract translation: 目的：提供具有除草活性的9-（5-异恶唑甲氧基苯基）亚氨基-8-硫杂-1,6-二氮杂双环（4.3.0）壬-7-酮衍生物和含有与活性成分相同的除草组合物。 该衍生物对水稻的稳定性高，除草效果好。 构型：9-（5-异恶唑甲氧基苯基）亚氨基-8-硫杂-1,6-二氮杂双环（4.3.0）壬-7-酮衍生物由式（1）表示，其中R是C1-C5烷基，苯基 基团或取代的苯基，其中取代的苯基具有选自C 1 -C 3烷氧基，卤素原子，氰基和羧酸酯基的取代基。 除草组合物的特征在于含有9-（5-异恶唑甲氧基苯基）亚氨基-8-硫杂-1,6-二氮杂双环（4.3.0）壬-7-酮衍生物作为活性成分。

公开(公告)号：KR1020040086696A

公开(公告)日：2004-10-12

申请号：KR1020030021052

申请日：2003-04-03

Applicant: 한국화학연구원

Inventor： 전동주 ,  김형래 ,  송종환 ,  장규환 ,  황인택

IPC: C07D405/12

Abstract: PURPOSE: Herbicidal2-(5-oxiranylmethoxyphenyl)-4,5,6,7-tetrahydro-2H-indazole derivatives are provided, which compounds have improved herbicidal effects and selectivity, so that the compounds can selectively kill weeds. CONSTITUTION: The herbicidal2-(5-oxiranylmethoxyphenyl)- 4,5,6,7-tetrahydro-2H-indazole derivatives represented by formula (1) are provided, wherein R1, R2 and R3 are independently hydrogen, C1-C5 alkyl, phenyl or substituted phenyl with 1 to 3 of halogen atoms. The method for preparing the herbicidal2-(5-oxiranylmethoxyphenyl)- 4,5,6,7-tetrahydro-2H-indazole derivatives of formula (1) comprises the steps of: reacting a compound of formula (2) with allyl halide in the presence of base to prepare a compound of formula (3); and introducing epoxy group into a double bond of the compound of formula (3), wherein X is halogen.

Abstract translation: 目的：提供除草剂2-（5-环氧乙烷基甲氧基苯基）-4,5,6,7-四氢-2H-吲唑衍生物，该化合物具有改善的除草效果和选择性，使得化合物可以选择性地杀死杂草。 构成：提供由式（1）表示的除草2-（5-环氧乙烷基甲氧基苯基）-4,5,6,7-四氢-2H-吲唑衍生物，其中R 1，R 2和R 3独立地是氢，C 1 -C 5烷基，苯基 或具有1至3个卤素原子的取代的苯基。 制备式（1）的除草-2-（5-环氧乙烷基甲氧基苯基）-4,5,6,7-四氢-2H-吲唑衍生物的方法包括以下步骤：使式（2）的化合物与烯丙基卤在 碱的存在以制备式（3）的化合物; 并将环氧基引入到式（3）化合物的双键中，其中X是卤素。

公开(公告)号：KR1020040017892A

公开(公告)日：2004-03-02

申请号：KR1020020049819

申请日：2002-08-22

Applicant: 한국화학연구원

Inventor： 유응걸 ,  전동주 ,  김형래 ,  송종환 ,  박관용 ,  하진열 ,  김진석

IPC: C07D495/04

Abstract: PURPOSE: Provided are derivatives of 9-(5-isoxazolinemethoxyphenyl)imino-8-thia-1.6-diazabicylco£4.3.0|nonane-7-one, represented by the formula(1) and herbicides containing them as active ingredients and having excellent herbicidal activity and selectivity when applied to a rice paddy. CONSTITUTION: Derivatives are represented by the formula(1), wherein R is C1-C6 alkyl, phenyl or substituted phenyl, wherein substituents are 1-3 of halogen atom, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, cyano, nitro, carboxyl and esters of carboxy acid.

Abstract translation: 目的：提供由式（1）表示的9-（5-异恶唑啉甲氧基苯基）亚氨基-8-硫杂-1,6-二氮杂双环[4.3.0]壬烷-7-酮和含有它们作为活性成分并具有优异的除草剂的衍生物 施用于水稻时的除草活性和选择性。 构成：衍生物由式（1）表示，其中R是C1-C6烷基，苯基或取代的苯基，其中取代基是1-3的卤素原子，C1-C3烷基，C1-C3烷氧基，C1-C3卤代烷基， 氰基，硝基，羧基和羧酸的酯。

公开(公告)号：KR1020030095677A

公开(公告)日：2003-12-24

申请号：KR1020020033207

申请日：2002-06-14

Applicant: 한국화학연구원

Inventor： 유응걸 ,  전동주 ,  김형래 ,  송종환 ,  박관용

IPC: C07D231/54

Abstract: PURPOSE: A process for preparing 3-chloro-2- (4-chloro-2-fluoro-5-hydroxyphenyl)- 4,5,6,7-tetrahydro-2H-indazole is provided, thereby improving its preparation yield and converting by-products of the preparation into starting material. CONSTITUTION: A process for preparing 3-chloro-2- (4-chloro-2-fluoro-5-hydroxyphenyl)- 4,5,6,7-tetrahydro-2H-indazole of the formula 1 comprises the steps of: reacting 2- (2-fluoro-4-chloro-5-hydroxyphenyl)- 2,3a,4,5,6,7- hexahydroindazole-3-one of the formula 2 with phosgene; concentrating the phosgene reaction mixture under reduced pressure; dissolving the concentrate in an organic solvent; adding ammonia water or hydroxide solution to the organic solvent and filtering solids; and distilling the filtrated solution, wherein the organic solvent is ethylacetate; the addition of ammonia water or hydroxide solution is carried out at room temperature; the solids are mainly constituted of a compound of the formula 2, and the by-products of the reaction include a dimer represented by the formula 3a, 3b or 3c.

Abstract translation: 目的：提供3-氯-2-（4-氯-2-氟-5-羟基苯基）-4,5,6,7-四氢-2H-吲唑的制备方法，从而提高其制备产率，并通过 - 制备成原料的产品。 构成：式1的3-氯-2-（4-氯-2-氟-5-羟基苯基）-4,5,6,7-四氢-2H-吲唑的制备方法包括以下步骤：使2 - （2-氟-4-氯-5-羟基苯基）-2,3a，4,5,6,7-六氢吲唑-3-酮与光气; 在减压下浓缩光气反应混合物; 将浓缩物溶解在有机溶剂中; 向有机溶剂中加入氨水或氢氧化物溶液并过滤固体; 并蒸馏过滤的溶液，其中有机溶剂是乙酸乙酯; 在室温下加入氨水或氢氧化钠溶液; 固体主要由式2的化合物构成，反应的副产物包括由式3a，3b或3c表示的二聚体。

公开(公告)号：KR100339708B1

公开(公告)日：2002-06-05

申请号：KR1019990007558

申请日：1999-03-08

Applicant: 한국화학연구원

Inventor： 유응걸 ,  송종환 ,  김형래 ,  전동주 ,  정정애 ,  김경만 ,  김태준

IPC: C07D413/12

Abstract: 본발명은하기화학식 1로표시되는 N-(5-이속사졸리닐메틸옥시페닐)-디메틸말레이미드유도체및 그의제조방법에관한것으로, 본발명의화합물은벼에대한안전성이탁월하고피 (ECHOR), 올챙이고랑이 (SCPJU), 물달개비 (MOOVA), 너도방동산이 (CYPSE), 올미 (SAGPY) 등의논 잡초에대해고루우수한제초활성을보이므로이양벼및 직파벼조건에서논 잡초용제초제로유용하게사용될수 있다. 상기식에서 R 은명세서에기재된바와같다.

公开(公告)号：KR1020020019750A

公开(公告)日：2002-03-13

申请号：KR1020000052917

申请日：2000-09-07

Applicant: 한국화학연구원

Inventor： 유응걸 ,  김형래 ,  전동주 ,  송종환 ,  김경만 ,  이정노 ,  김형철 ,  홍경식

IPC: A01N43/80

CPC classification number: A01N43/80

Abstract: PURPOSE: Provided is 5-benzyloxymethyl-1,2-isoxazoline derivative which has an excellent herbicidal activity. Also, provided are its manufacturing method and herbicides containing the derivative as an active ingredient. CONSTITUTION: 5-benzyloxymethyl-1,2-isoxazoline derivative is represented by the formula(I), wherein X1, X2 and X3 individually represent hydrogen, methyl group, ethyl group, halogen group, methoxy group or nitro group (provided that it is an exception that X1, X2 and X3 are decimals all together); Y1, Y2 and Y3 are individually hydrogen or fluorine.

Abstract translation: 目的：提供具有优异除草活性的5-苄氧基甲基-1,2-异恶唑啉衍生物。 此外，其制造方法和含有该衍生物作为活性成分的除草剂。 构成：5-苄氧基甲基-1,2-异恶唑啉衍生物由式（I）表示，其中X1，X2和X3各自表示氢，甲基，乙基，卤素基，甲氧基或硝基（条件是它是 一个例外，X1，X2和X3都是小数） Y1，Y2和Y3分别为氢或氟。

公开(公告)号：KR100241260B1

公开(公告)日：2000-03-02

申请号：KR1019970065412

申请日：1997-12-02

Applicant: 한국화학연구원

Inventor： 유응걸 ,  김경만 ,  송종환 ,  황인택 ,  이수영 ,  김형래 ,  양순모

IPC: C07D215/32

Abstract: 본 발명은 제초활성을 갖는 화학식 1의 O-퀴놀리닐아미드옥심 유도체, 그의 제조방법 및 그를 포함하는 제초제 조성물에 관한 것이다.

(상기 식에서, R 은 명세서에서 정의한 바와 같다.)
상기 화학식 1의 O-퀴놀리닐아미드옥심 유도체 및 그를 유효성분으로 함유하는 조성물은 제초제 또는 식물생장 억제제로 유용하게 사용될 수 있다.